Ammonia → 7beta-amino-3-[(1-benzylideneamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid

HRID 483021Notes

Reaction equation

HRID 483021 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[CH:19](=[N:26][N:27]1[C:31]([SH:32])=[N:30][N:29]=[N:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CS(O)(=O)=O.N>C(#N)C.O>[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:32][C:31]3[N:27]([N:26]=[CH:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:28]=[N:29][N:30]=3)[CH2:15][S:14][C@H:9]12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6395Methanesulfonic AcidHCID 4413287-Aminocephalosporanic acidHCID 178527993HCID 178527993, compound

Product 1

HCID 1317145567beta-amino-3-[(1-benzylideneamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acidYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

10.9 g of 7β-aminocephalosporanic acid and 8.2 g of 1-benzylideneamino-5-mercapto-1H-tetrazole were dissolved in 60 ml of acetonitrile, and 19.2 g of methanesulfonic acid were added gradually thereto at a temperature below 30° C. The mixture was stirred at room temperature for 30 minutes and then at 44° C. for 4 hours. After ice-cooling, 400 ml of water were added to the reaction mixture, and said mixture was adjusted to 5.2 with 28% ammonia. The resultant precipitates were collected by filtration, washed with water and tetrahydrofuran, and then dried. 11.53 g of 7β-amino-3-[(1-benzylideneamino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid were obtained as pale yellow powder. mp 170° C. (decomp.)

Workup

  1. customat a temperature below 30° C
  2. waitat 44° C. for 4 hours
  3. temperatureAfter ice-cooling
  4. customThe resultant precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water and tetrahydrofuran
  7. customdried

Sources & evidence

ORD record
ord-d0e8fe4e927043379ddac0db9aa8ffe8
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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